Photo by Ryan Arguillo

Holiday Homes in Winona

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Featured Holiday Homes in Winona

Our top choices for Winona holiday homes

Hillside Home: Amazing Views w/ Big Deck 5 Min. From Downtown + Trailheads!
Exterior

Hillside Home: Amazing Views w/ Big Deck 5 Min. From Downtown + Trailheads!

9.8 out of 10, Exceptional, (42)
"This place is a great spot to relax and unwind. "
The price is AU$495
includes taxes & fees
1 Sept - 2 Sept
Hillside Home: Amazing Views w/ Big Deck 5 Min. From Downtown + Trailheads!
The Rock House is a cozy and luxurious getaway
Outdoor dining

The Rock House is a cozy and luxurious getaway

10.0 out of 10, Exceptional, (48)
"This property is in a great location, clean and so cute. Would definitely recommend staying here."
The price is AU$519
includes taxes & fees
8 Sept - 9 Sept
The Rock House is a cozy and luxurious getaway
Mountain View Retreat Close to Downtown Flagstaff, Big Deck, Trails Nearby!
Exterior

Mountain View Retreat Close to Downtown Flagstaff, Big Deck, Trails Nearby!

9.6 out of 10, Exceptional, (157)
"The house was very clean and well maintained. Would definitely stay again!"
Mountain View Retreat Close to Downtown Flagstaff, Big Deck, Trails Nearby!
Quaint Historic Downtown Flagstaff Hideaway
Fridge, microwave, oven, stovetop

Quaint Historic Downtown Flagstaff Hideaway

9.8 out of 10, Exceptional, (282)
"The home was perfect for our needs and in a perfect location. Really close to downtown, loved walking around town. The backyard is very spacious "
Quaint Historic Downtown Flagstaff Hideaway
Country Club Bungalow, Sleeps 4
Smart TV, fireplace, DVD player

Country Club Bungalow, Sleeps 4

10.0 out of 10, Exceptional, (22)
"Very nice place to stay"
Country Club Bungalow, Sleeps 4
Town Home in the Pine Trees - Sleeps 5!
Fridge, microwave, oven, stovetop

Town Home in the Pine Trees - Sleeps 5!

10.0 out of 10, Exceptional, (46)
"Great spot in flag, very roomy and great price!"
Town Home in the Pine Trees - Sleeps 5!
Charming Hideaway in Downtown Flagstaff
Terrace/patio

Charming Hideaway in Downtown Flagstaff

9.6 out of 10, Exceptional, (404)
"Excellent location to local attractions."
Charming Hideaway in Downtown Flagstaff
SUMMER SALE! Ultimate Group Gathering - 6bd 5bth in Flagstaff on National Forest
Interior

SUMMER SALE! Ultimate Group Gathering - 6bd 5bth in Flagstaff on National Forest

9.8 out of 10, Exceptional, (200)
"Good for our large group and convenient to several activity locations in and around Flagstaff."
SUMMER SALE! Ultimate Group Gathering - 6bd 5bth in Flagstaff on National Forest
Historic Dowtown Home. Walk To shops, Restaurants, NAU
Terrace/patio

Historic Dowtown Home. Walk To shops, Restaurants, NAU

9.8 out of 10, Exceptional, (425)
"Hotel and area are great but getting around Flagstaff is troublesome."
Historic Dowtown Home. Walk To shops, Restaurants, NAU
Cozy retreat close to trails, downtown & NAU - Pet Friendly - Sleeps 9
Fridge, microwave, oven, stovetop

Cozy retreat close to trails, downtown & NAU - Pet Friendly - Sleeps 9

9.8 out of 10, Exceptional, (218)
"Clean, roomy but cozy!!!Our second time staying, will come again!"
Cozy retreat close to trails, downtown & NAU - Pet Friendly - Sleeps 9
Gorgeous Presidio in the Pines home with many upgrades & comforts for your stay
Fridge, microwave, oven, stovetop

Gorgeous Presidio in the Pines home with many upgrades & comforts for your stay

9.8 out of 10, Exceptional, (52)
"Everything was as shown…it was excellent. "
The price is AU$784
includes taxes & fees
7 Sept - 8 Sept
Gorgeous Presidio in the Pines home with many upgrades & comforts for your stay
Eclectic & Fun Lumberyard Urban Cabin #1 in downtown, next to NAU
Fridge, microwave, oven, stovetop

Eclectic & Fun Lumberyard Urban Cabin #1 in downtown, next to NAU

9.8 out of 10, Exceptional, (23)
"Perfect size for our group. Location was great when it came to walking to restaurants and Main Street. Close to campus which made sound levels a little loud but nothing too crazy. Loved our stay!!"
The price is AU$355
includes taxes & fees
1 Sept - 2 Sept
Eclectic & Fun Lumberyard Urban Cabin #1 in downtown, next to NAU
Adorable 2 bedroom guesthouse in the pines
Terrace/patio

Adorable 2 bedroom guesthouse in the pines

9.8 out of 10, Exceptional, (71)
"Great location, very clean, great backyard for dogs. We will definitely stay again. "
Adorable 2 bedroom guesthouse in the pines
AC & GAME ROOM! Pondy Hills Flagstaff Getaway
Fridge, microwave, oven, stovetop

AC & GAME ROOM! Pondy Hills Flagstaff Getaway

9.8 out of 10, Exceptional, (24)
"All was great "
The price is AU$829
includes taxes & fees
1 Sept - 2 Sept
AC & GAME ROOM! Pondy Hills Flagstaff Getaway
Downtown Flagstaff Bungalow - 5 minute walk to downtown
Property grounds

Downtown Flagstaff Bungalow - 5 minute walk to downtown

10.0 out of 10, Exceptional, (356)
"We loved our stay at this beautiful home. Very comfortable and cozy and convenient to beautiful downtown. Will be staying there again for sure."
Downtown Flagstaff Bungalow - 5 minute walk to downtown
NEW! HOT TUB/BBQ/Games/Park in the prestigious Presidio Pines!
Exterior

NEW! HOT TUB/BBQ/Games/Park in the prestigious Presidio Pines!

10.0 out of 10, Exceptional, (4)
"Wonderful location and the house is very well appointed, great outside area to enjoy the fantastic weather!!"
NEW! HOT TUB/BBQ/Games/Park in the prestigious Presidio Pines!
A Perfect Vacation Home! Trail Access, Central A/C, Pets Welcome, TOP Reviewed!
Outdoor dining

A Perfect Vacation Home! Trail Access, Central A/C, Pets Welcome, TOP Reviewed!

10.0 out of 10, Exceptional, (348)
"Very nice home "
A Perfect Vacation Home! Trail Access, Central A/C, Pets Welcome, TOP Reviewed!
Flagstaff Ponderosa Pines
Exterior

Flagstaff Ponderosa Pines

9.6 out of 10, Exceptional, (23)
"This cute home is located in a great area of Flagstaff, it’s nicely furnished, very welcoming and the hosts are super to work with. Would definitely stay again. "
Flagstaff Ponderosa Pines
Blushing Bungalow w/AC, Fenced Yard, W/D, Garage, Speedy WiFi, 3 Smart TVs.
Interior

Blushing Bungalow w/AC, Fenced Yard, W/D, Garage, Speedy WiFi, 3 Smart TVs.

9.8 out of 10, Exceptional, (30)
"Very clean lodging in a great location. Easy access to downtown and other attractions. All the comforts of home."
Blushing Bungalow w/AC, Fenced Yard, W/D, Garage, Speedy WiFi, 3 Smart TVs.
New! Fairway Fun: Big Deck, Arcade, AC & Views
Outdoor dining

New! Fairway Fun: Big Deck, Arcade, AC & Views

10.0 out of 10, Exceptional, (1)
"What an incredible host and property. The attention to details was perfect. Everything was as described in the listing, clean and functional."
New! Fairway Fun: Big Deck, Arcade, AC & Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winona Hotel Reviews

Find out more about Winona

Find out more about Winona

Winona Holiday Homes information

Number of reviews
Accommodation
921 Holiday Homes
Lowest Price
AU$355
Highest Price
AU$829

Explore a world of travel with Expedia

Explore a world of travel with Expedia